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Phenolic group on A-ring is key for dracoflavan B as a selective noncompetitive inhibitor of α-amylase.

Abstract：

:A high throughput assay was applied to guide the isolation of a new pancreatic α-amylase inhibitor, dracoflavan B, from the dragon's blood resin from Daemonorops draco. Applying C18 column, we successfully isolated both diastereomers and their structures verified by (1)H NMR spectra in comparison with the literature values. Their activity in inhibition of pancreatic α-amylase with comparable IC50 values of 23μM (A type) and 27μM (B type) that are similar to that of acarbose. Dracoflavan B shows much weaker activity in inhibiting bacterial α-amylase and no activity towards fungal α-amylase. Moreover, both isomers show no inhibitory activity towards mammalian α-glucosidase. Kinetic analysis revealed that using starch as the substrate, dracoflavan B was a non-competitive α-amylase inhibitor with a Ki value of 11.7μM. Lack of α-amylase inhibition for proanthocyanidin A2 dimer demonstrated that dracoflavan B hydrophobic nature of the B, A', C' and B' rings are important for its α-amylase inhibition. In addition, selective chemical modification studies revealed that the phenolic group is also vital to dracoflavan B for its pancreatic α-amylase inhibition activity. Without the A ring phenolic hydrogen bond donor, the derivatives of dracoflavan B showed detrimental α-amylase inhibition. On the contrary, galloylation on the A ring phenolic OH group enhanced the activity as shown by the low IC50 (12μM) against α-amylase which is 56% more potent as compared to dracoflavan B.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Toh ZS,Wang H,Yip YM,Lu Y,Lim BJ,Zhang D,Huang D

doi

10.1016/j.bmc.2015.11.008

subject

Has Abstract

pub_date

2015-12-15 00:00:00

pages

7641-9

issue

24

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)30133-4

journal_volume

23

pub_type

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